title: Conformational analysis of the anti-obesity drug lorcaserin in water: how to take advantage of long-range residual dipolar couplings.
abstract: The conformational state of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (lorcaserin) in water has been determined on the basis of one-bond and long-range C-H residual dipolar coupling (RDC) data along with DFT computations and (3)J(HH) coupling-constant analysis. According to this analysis, lorcaserin exists as a conformational equilibrium of two crown-chair forms, of which the preferred conformation has the methyl group in an equatorial orientation.
authors.affiliation: Departamento de Química Orgánica, Universidade de Vigo, Campus Lagoas-Marcosende, 36310 Vigo (Spain), Fax: (+34) 986812262; Departamento de Química Orgánica, Universidade de Santiago de Compostela, Campus Vida, 15782, Santiago de Compostela (Spain); Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS), Universidade de Santiago de Compostela, Campus Vida, 15782, Santiago de Compostela (Spain), Fax: (+34) 881815704; Department of Chemistry, Carnegie Mellon University, 4400 Fifth Ave, Pittsburg, PA (USA).
authors.forename: Pablo
authors.initials: P
authors.lastname: Trigo-Mouriño
authors.forename: M Carmen
authors.initials: MC
authors.lastname: de la Fuente
authors.forename: Roberto R
authors.initials: RR
authors.lastname: Gil
authors.forename: Víctor M
authors.initials: VM
authors.lastname: Sánchez-Pedregal
authors.forename: Armando
authors.initials: A
authors.lastname: Navarro-Vázquez
mesh_terms: D019440:Anti-Obesity Agents / Q000737:chemistry* / Q000494:pharmacology; D001552:Benzazepines / Q000737:chemistry*; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D019906:Nuclear Magnetic Resonance, Biomolecular; D014867:Water / Q000737:chemistry*
chemical_list: D019440:Anti-Obesity Agents; D001552:Benzazepines; D014867:Water; C506658:lorcaserin
keywords: NMR spectroscopy; anti-obesity drugs; conformation analysis; residual dipolar couplings